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Re: Dock vs. mooring
On the subject of moorings and pump-outs: In the Old Saybrook/Old Lyme, Connecticut area, the pump-out boat will give you an orange flag to attach to your bow rail if you're in need of a pump-out but not going to be aboard (along with a container for a tip). This is ideal for folks on moorings and in slips as not too many marinas really want to deal with the pump-out directly (as there is a large State-run pump-out just north of the railroad bridge).
I agree with the earlier comment that access to water is an important consideration and I think especially so if your doing multiple overnights regularly.